Abstract
In contrast to achiral hydrophilic interaction liquid chromatography (HILIC), which is a popular and largely applied technique to analyze polar compounds such as pharmaceuticals, metabolites, proteins, peptides, amino acids, oligonucleotides, and carbohydrates, the introduction of the HILIC concept in enantioselective chromatography has been relatively recent and scarcely debated. In this chapter, the HILIC enantioseparations carried out on polysaccharide-based chiral stationary phases are grouped and discussed. Another objective of this chapter is to provide a comprehensive overview and insight into the experimental conditions needed to operate under HILIC mode. Finally, to stimulate and facilitate the application of this chromatographic technique, a detailed experimental protocol of a chiral resolution on a chlorinated cellulose-based chiral stationary phase under HILIC conditions is described.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Hemström P, Irgum K (2006) Hydrophilic interaction chromatography. J Sep Sci 29:1784–1821
Jandera P (2011) Stationary and mobile phases in hydrophilic interaction chromatography: a review. Anal Chim Acta 692:1–25
Schuster G, Lindner W (2013) Comparative characterization of hydrophilic interaction liquid chromatography columns by linear solvation energy relationships. J Chromatogr A 1273:73–94
Guo Y (2015) Recent progress in the fundamental understanding of hydrophilic interaction chromatography (HILIC). Analyst 140:6452–6466
McCalley DV (2017) Understanding and manipulating the separation in hydrophilic interaction liquid chromatography. J Chromatogr A 1523:49–71
Felinger CA (2013) A hydrophilic interaction liquid chromatography. In: Fanali S et al (eds) Liquid chromatography: fundamentals and instrumentation. Elsevier, Amsterdam, pp 19–40
Linden JC, Lawhead CL (1975) Liquid chromatography of saccharides. J Chromatogr 105:125–133
Palmer JK (1975) A versatile system for sugar analysis via liquid chromatography. Anal Lett 8:215–224
Alpert AJ (1990) Hydrophilic-interaction chromatography for the separation of peptides, nucleic acids and other polar compounds. J Chromatogr 499:177–196
Dejaegher B, Vander Heyden Y (2010) HILIC methods in pharmaceutical analysis. J Sep Sci 33:698–715
Lämmerhofer M (2010) HILIC and mixed-mode chromatography: the rising stars in separation science HILIC and mixed-mode chromatography. J Sep Sci 33:679–680
Jandera P (2008) Stationary phases for hydrophilic interaction chromatography, their characterization and implementation into multidimensional chromatography concepts. J Sep Sci 31:1421–1437
Okamoto Y, Yashima E (1998) Polysaccharide derivatives for chromatographic separation of enantiomers. Angew Chem Int Ed Engl 37:1020–1043
Cavazzini A, Pasti L, Massi A, Marchetti N, Dondi F (2011) Recent applications in chiral high performance liquid chromatography: a review. Anal Chim Acta 706:205–222
Lämmerhofer M (2010) Chiral recognition by enantioselective liquid chromatography: mechanisms and modern chiral stationary phases. J Chromatogr A 1217:814–856
Ikai T, Okamoto Y (2009) Structure control of polysaccharide derivatives for efficient separation of enantiomers by chromatography. Chem Rev 109:6077–6101
Chankvetadze B (2012) Recent developments on polysaccharide-based chiral stationary phases for liquid-phase separation of enantiomers. J Chromatogr A 1269:26–51
Okamoto Y, Kawashima M, Hatada K (1984) Useful chiral packing materials for high-performance liquid chromatographic resolution of enantiomers: phenylcarbamates of polysaccharides coated on silica gel. J Am Chem Soc 106:5357–5359
Pierini M, Carradori S, Menta S, Secci D, Cirilli R (2017) 3-(Phenyl-4-oxy)-5-phenyl-4,5-dihydro-(1H)-pyrazole: a fascinating molecular framework to study the enantioseparation ability of the amylose (3,5-dimethylphenylcarbamate) chiral stationary phase. Part II. Solvophobic effects in enantiorecognition process. J Chromatogr A 1499:140–148
Ortuso F, Alcaro S, Menta S, Fioravanti R, Cirilli R (2014) A chromatographic and computational study on the driving force operating in the exceptionally large enantioseparation of N-thiocarbamoyl-3-(4′-biphenyl)-5-phenyl-4,5-dihydro-(1H) pyrazole on a 4-methylbenzoate cellulose-based chiral stationary phase. J Chromatogr A 1324:71–77
Cirilli R, Simonelli A, Ferretti R, Bolasco A, Chimenti P, Secci D, Maccioni E, La Torre F (2006) Analytical and semipreparative high performance liquid chromatography enantioseparation of new substituted 1-thiocarbamoyl-3,5-diaryl-4,5-dihydro-(1H)-pyrazoles on polysaccharide-based chiral stationary phases in normal-phase, polar organic and reversed-phase conditions. J Chromatogr A 101:198–203
Sanna ML, Maccioni E, Vigo S, Faggi C, Cirilli R (2010) Application of an immobilised amylose-based chiral stationary phase to the development of new monoamine oxidase B inhibitors. Talanta 82:426–431
Tachibana K, Ohnishi A (2001) Reversed-phase liquid chromatographic separation of enantiomers on polysaccharide type chiral stationary phases. J Chromatogr A 906:127–154
Zhang T, Nguyen D, Franco P (2010) Reversed-phase screening strategies for liquid chromatography on polysaccharide-derived chiral stationary phases. J Chromatogr A 1217:1048–1055
Younes AA, Mangelings D, Vander Heyden Y (2012) Chiral separations in reversed-phase liquid chromatography: evaluation of several polysaccharide-based chiral stationary phases for a separation strategy update. J Chromatogr A 1269:154–167
Rizzo S, Menta S, Benincori T, Ferretti R, Pierini M, Cirilli R, Sannicolò F (2015) Determination of the enantiomerization barrier of the residual enantiomers of C3-symmetric tris[3-(1-methyl-2-alkyl)indolyl]phosphane oxides: case study of a multitasking HPLC investigation based on an immobilized polysaccharide stationary phase. Chirality 12:888–899
Ferretti R, Gallinella B, La Torre F, Zanitti L, Turchetto L, Mosca A, Cirilli R (2009) Direct high-performance liquid chromatography enantioseparation of terazosin on an immobilised polysaccharide-based chiral stationary phase under polar organic and reversed-phase conditions. J Chromatogr A 1216:5385–5390
Cirilli R, Ferretti R, Gallinella B, De Santis E, Zanitti L, La Torre F (2008) High-performance liquid chromatography enantioseparation of proton pump inhibitors using the immobilized amylose-based Chiralpak IA chiral stationary phase in normal-phase, polar organic and reversed-phase conditions. J Chromatogr A 1177:105–113
Cirilli R, Ferretti R, De Santis E, Gallinella B, Zanitti L, La Torre F (2008) High-performance liquid chromatography separation of enantiomers of flavanone and 2′-hydroxychalcone under reversed-phase conditions. J Chromatogr A 1190:95–101
Kummer M, Werner G (1998) Chiral resolution of enantiomeric steroids by high-performance liquid chromatography on amylose tris(3,5-dimethylphenylcarbamate) under reversed-phase conditions. J Chromatogr A 825:107–114
Chankvetadze B, Yamamoto C, Okamoto Y (2001) Enantioseparation of selected chiral sulfoxides using polysaccharide-type chiral stationary phases and polar organic, polar aqueous–organic and normal-phase eluents. J Chromatogr A 922:127–137
Jibuti G, Mskhiladze A, Takaishvili N, Karchkhadze M, Chankvetadze L, Farkas T, Chankvetadze B (2012) HPLC separation of dihydropyridine derivatives enantiomers with emphasis on elution order using polysaccharide-based chiral columns. J Sep Sci 35:2529–2537
Cirilli R, Ferretti R, Gallinella B, Zanitti L (2013) Retention behavior of proton pump inhibitors using immobilized polysaccharide-derived chiral stationary phases with organic-aqueous mobile phases. J Chromatogr A 1304:147–153
Materazzo S, Carradori S, Ferretti R, Gallinella B, Secci D, Cirilli R (2014) Effect of the water content on the retention and enantioselectivity of albendazole and fenbendazole sulfoxides using amylose-based chiral stationary phases in organic-aqueous conditions. J Chromatogr A 1327:73–79
Gallinella B, Bucciarelli L, Zanitti L, Ferretti R, Cirilli R (2014) Direct separation of the enantiomers of oxaliplatin on a cellulose-based chiral stationary phase in hydrophilic interaction liquid chromatography mode. J Chromatogr A 1339:210–213
Matarashvili I, Ghughunishvili D, Chankvetadze L, Takaishvili N, Khatiashvili T, Tsintsadze M, Farkasc T, Chankvetadze B (2017) Separation of enantiomers of chiral weak acids with polysaccharide-based chiral columns and aqueous-organic mobile phases in high-performance liquid chromatography: typical reversed-phase behavior? J Chromatogr A 1483:86–62
Ferretti R, Carradori S, Guglielmi P, Pierini M, Casulli A, Cirilli R (2017) Enantiomers of triclabendazole sulfoxide: analytical and semipreparative HPLC separation, absolute configuration assignment, and transformation into sodium salt. J Pharm Biomed Anal 40:38–44
Ferretti R, Zanitti L, Casulli A, Cirilli R (2016) Green high-performance liquid chromatography enantioseparation of lansoprazole using a cellulose-based chiral stationary phase under ethanol/water mode. J Sep Sci 39:1418–1424
Thirupathi C, Nagesh Kumar K, Srinivasu G, Lakshmi Narayana C, Parameswara Murthy C (2018) Development and validation of stereo selective method for the separation of razoxane enantiomers in hydrophilic interaction chromatography. J Chromatogr Sci 56:147–153
Cirilli R, Guglielmi P, Formica FR, Casulli A, Carradori S (2017) The sodium salt of the enantiomers of ricobendazole: preparation, solubility and chiroptical properties. J Pharm Biomed Anal 139:1–7
Ferretti R, Zanitti L, Casulli A, Cirilli R (2018) Unusual retention behavior of omeprazole and its chiral impurities B and E on the amylose tris (3-chloro-5-methylphenylcarbamate) chiral stationary phase in polar organic mode. J Pharmaceut Anal 8(4):234–239. https://doi.org/10.1016/j.jpha.2018.04.001
Wu Z, Razzak M, Tucker IG, Medlicott NJ (2005) Physicochemical characterization of ricobendazole: I. Solubility, lipophilicity, and ionization characteristics. J Pharm Sci 94:983–993
Ferretti R, Mai A, Gallinella B, Zanitti L, Valente S, Cirilli R (2011) Application of 3 μm particle-based amylose-derived chiral stationary phases for the enantioseparation of potential histone deacetylase inhibitors. J Chromatogr A 1218:8394–8398
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2019 Springer Science+Business Media, LLC, part of Springer Nature
About this protocol
Cite this protocol
Cirilli, R. (2019). HPLC Enantioseparations with Polysaccharide-Based Chiral Stationary Phases in HILIC Conditions. In: Scriba, G.K.E. (eds) Chiral Separations. Methods in Molecular Biology, vol 1985. Humana, New York, NY. https://doi.org/10.1007/978-1-4939-9438-0_7
Download citation
DOI: https://doi.org/10.1007/978-1-4939-9438-0_7
Publisher Name: Humana, New York, NY
Print ISBN: 978-1-4939-9437-3
Online ISBN: 978-1-4939-9438-0
eBook Packages: Springer Protocols